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3 H ‐Indol‐3‐ols by a novel ring contraction
Author(s) -
Lednicer Daniel,
Emmert D. Edward
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070316
Subject(s) - chemistry , alkylation , ring (chemistry) , liquid ammonia , amide , tribromide , potassium , medicinal chemistry , contraction (grammar) , ammonia , base (topology) , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics , medicine
Treatment of α‐hydroxy‐α‐phenyl‐ o ‐toluidide with phosphorus tribromide afforded a series of 4 H ‐3,1‐benzoxazines. These last, when reacted with potassium amide in liquid ammonia, ring contracted to 2,3‐disubstituted 3 H ‐indol‐3‐ols. The scope of this rearrangement was examined. The indolols on treatment with hot base were found to rearrange to indoxyls. Several of these as well as their N ‐alkylation products are described.